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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 15:47:32 UTC
HMDB IDHMDB0015447
Secondary Accession Numbers
  • HMDB15447
Metabolite Identification
Common NamePenbutolol
DescriptionPenbutolol is only found in individuals that have used or taken this drug. It is a medication in the class of beta blockers, used in the treatment of high blood pressure. [Wikipedia ]Penbutolol competes with adrenergic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart and vascular smooth muscle and beta(2)-receptors in the bronchial and vascular smooth muscle. Beta(1)-receptor blockade results in a decrease in resting and exercise heart rate and cardiac output, a decrease in both systolic and diastolic blood pressure, and, possibly, a reduction in reflex orthostatic hypotension.
Structure
Data?1582753298
Synonyms
ValueSource
LevatolHMDB
Hoe-893DHMDB
Penbutolol sulfateHMDB
BetapressinHMDB
Hoe893dHMDB
Sulfate, penbutololHMDB
Hoe 893DHMDB
Penbutolol sulfate (2:1)HMDB
Chemical FormulaC18H29NO2
Average Molecular Weight291.4284
Monoisotopic Molecular Weight291.219829177
IUPAC Name(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol
Traditional Name(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol
CAS Registry Number36507-48-9
SMILES
CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1
InChI Identifier
InChI=1S/C18H29NO2/c1-18(2,3)19-12-15(20)13-21-17-11-7-6-10-16(17)14-8-4-5-9-14/h6-7,10-11,14-15,19-20H,4-5,8-9,12-13H2,1-3H3/t15-/m0/s1
InChI KeyKQXKVJAGOJTNJS-HNNXBMFYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.021 g/LNot Available
LogP4.15HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP10(3.84) g/LALOGPS
logP10(3.55) g/LChemAxon
logS10(-4.1) g/LALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity86.6 m³·mol⁻¹ChemAxon
Polarizability34.58 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.75431661259
DarkChem[M-H]-165.8931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PenbutololCC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC12747.1Standard polar33892256
PenbutololCC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC12137.0Standard non polar33892256
PenbutololCC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC12157.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Penbutolol,1TMS,isomer #1CC(C)(C)NC[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C2116.8Semi standard non polar33892256
Penbutolol,1TMS,isomer #2CC(C)(C)N(C[C@H](O)COC1=CC=CC=C1C1CCCC1)[Si](C)(C)C2301.2Semi standard non polar33892256
Penbutolol,2TMS,isomer #1CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C)[Si](C)(C)C2347.0Semi standard non polar33892256
Penbutolol,2TMS,isomer #1CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C)[Si](C)(C)C2443.1Standard non polar33892256
Penbutolol,2TMS,isomer #1CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C)[Si](C)(C)C2590.0Standard polar33892256
Penbutolol,1TBDMS,isomer #1CC(C)(C)NC[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C(C)(C)C2331.2Semi standard non polar33892256
Penbutolol,1TBDMS,isomer #2CC(C)(C)N(C[C@H](O)COC1=CC=CC=C1C1CCCC1)[Si](C)(C)C(C)(C)C2555.6Semi standard non polar33892256
Penbutolol,2TBDMS,isomer #1CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2818.2Semi standard non polar33892256
Penbutolol,2TBDMS,isomer #1CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2891.4Standard non polar33892256
Penbutolol,2TBDMS,isomer #1CC(C)(C)N(C[C@@H](COC1=CC=CC=C1C1CCCC1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2785.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Penbutolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-07jr-9670000000-a79fb91d287e7cfdc7512017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Penbutolol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9723000000-f4da418202c281b26d1c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Penbutolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 10V, Positive-QTOFsplash10-0006-2290000000-ace7f5ff44fdb9b5b7912016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 20V, Positive-QTOFsplash10-000i-9570000000-00b3838f0255ecd5c8232016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 40V, Positive-QTOFsplash10-00dr-9200000000-cebecfe8b8e40ed053bd2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 10V, Negative-QTOFsplash10-01ox-1790000000-ca08d570c87a1a04dad12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 20V, Negative-QTOFsplash10-03di-1900000000-d9272a3fe0f9ad9dbffe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 40V, Negative-QTOFsplash10-03xu-8900000000-2e9694efe38bd6f12d892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 10V, Positive-QTOFsplash10-0006-2090000000-64af498c50d53a85c9da2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 20V, Positive-QTOFsplash10-00ko-3390000000-f73c88fee4aee3b02b3f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 40V, Positive-QTOFsplash10-0a4i-9200000000-5d04f85a5d512559ca562021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 10V, Negative-QTOFsplash10-01ox-0790000000-19293d327932c94fb42c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 20V, Negative-QTOFsplash10-03di-0910000000-b2fd879060ccb5ebf5632021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Penbutolol 40V, Negative-QTOFsplash10-02tc-8900000000-992ab80beaa1f50314302021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01359 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01359 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01359
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID34369
KEGG Compound IDC07416
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPenbutolol
METLIN IDNot Available
PubChem Compound37464
PDB IDNot Available
ChEBI ID354975
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hjorth S: (-)-Penbutolol as a blocker of central 5-HT1A receptor-mediated responses. Eur J Pharmacol. 1992 Nov 3;222(1):121-7. [PubMed:1468487 ]
  2. Martinez Jorda R, Aguirre C, Calvo R, Rodriguez-Sasiain JM, Erill S: Decrease in penbutolol central response as a cause of changes in its serum protein binding. J Pharm Pharmacol. 1990 Mar;42(3):164-6. [PubMed:1974610 ]
  3. Frishman WH, Covey S: Penbutolol and carteolol: two new beta-adrenergic blockers with partial agonism. J Clin Pharmacol. 1990 May;30(5):412-21. [PubMed:2189902 ]
  4. Pepe S, Scalici G, D'Angelo A, Curiale B, Corrao S, Agnello C: [Validity of the use of penbutolol in essential arterial hypertension]. Minerva Med. 1990 Jun;81(6):471-3. [PubMed:2359502 ]
  5. Aguirre C, Rodriguez-Sasiain JM, Calvo R: Decrease in penbutolol protein binding as a consequence of treatment with some alkylating agents. Cancer Chemother Pharmacol. 1994;34(1):86-8. [PubMed:8174208 ]
  6. Maurer HH, Tenberken O, Kratzsch C, Weber AA, Peters FT: Screening for library-assisted identification and fully validated quantification of 22 beta-blockers in blood plasma by liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization. J Chromatogr A. 2004 Nov 26;1058(1-2):169-81. [PubMed:15595665 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
References
  1. Venter CP, Joubert PH: Ethnic differences in beta-1-adrenoceptor sensitivity. S Afr Med J. 1982 Nov 27;62(23):849-50. [PubMed:6755764 ]
  2. Sanchez C: Effect of serotonergic drugs on footshock-induced ultrasonic vocalization in adult male rats. Behav Pharmacol. 1993 Jun;4(3):269-277. [PubMed:11224195 ]
  3. Doze P, Elsinga PH, Maas B, Van Waarde A, Wegman T, Vaalburg W: Synthesis and evaluation of radiolabeled antagonists for imaging of beta-adrenoceptors in the brain with PET. Neurochem Int. 2002 Feb;40(2):145-55. [PubMed:11738481 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
References
  1. Kulkarni RD, DaSilva LM, Chabria NL, Chadha DR: Beta-2 adrenoceptor blocking activity of penbutolol and propranolol at very low doses. Clin Pharmacol Ther. 1977 Jun;21(6):685-90. [PubMed:16716 ]
  2. Hjorth S, Sharp T: In vivo microdialysis evidence for central serotonin1A and serotonin1B autoreceptor blocking properties of the beta adrenoceptor antagonist (-)penbutolol. J Pharmacol Exp Ther. 1993 May;265(2):707-12. [PubMed:8098761 ]
  3. Hjorth S, Bengtsson HJ, Milano S: Raphe 5-HT1A autoreceptors, but not postsynaptic 5-HT1A receptors or beta-adrenoceptors, restrain the citalopram-induced increase in extracellular 5-hydroxytryptamine in vivo. Eur J Pharmacol. 1996 Nov 28;316(1):43-7. [PubMed:8982649 ]
  4. Sanchez C: Effect of serotonergic drugs on footshock-induced ultrasonic vocalization in adult male rats. Behav Pharmacol. 1993 Jun;4(3):269-277. [PubMed:11224195 ]
  5. Ijzerman AP, Nagesser A, Garritsen A: The membrane stabilizing activity of beta-adrenoceptor ligands. Quantitative evaluation of the interaction of phenoxypropanolamines with the [3H]batrachotoxinin A 20-alpha-benzoate binding site on voltage-sensitive sodium channels in rat brain. Biochem Pharmacol. 1987 Dec 15;36(24):4239-44. [PubMed:2446632 ]